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Open Access Publications from the University of California

4-iminocyclobutenones: Synthesis and building-blocks of aminohydroquinones and annulated quinolines

  • Author(s): Oppermann, G
  • Stranberg, M
  • Moore, HW
  • Schaumann, E
  • Adiwidjaja, G
  • et al.

Two methods are presented for the synthesis of the title compounds starting from cyclobutenediones: an alkoxide substitution approach and a Staudinger reaction. Unsaturated lithiumorganyls may be added to the remaining carbonyl group and on heating lead to ring enlargement in a cascading process. 4-Alkenyl or 4-aryl derivatives yield aminophenols or -naphthols; 4-alkynyl compounds give cyclopenta-annulated quinolines. © Georg Thieme Verlag Stuttgart.

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